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class="mw-page-title-main">Prodrug</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 34 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-34" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">34 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AF%D9%88%D8%A7%D8%A1_%D8%A3%D9%88%D9%84%D9%8A" title="دواء أولي – Arabic" lang="ar" hreflang="ar" data-title="دواء أولي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Prof%C3%A0rmac" title="Profàrmac – Catalan" lang="ca" hreflang="ca" data-title="Profàrmac" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Prodrug" title="Prodrug – Danish" lang="da" hreflang="da" data-title="Prodrug" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Prodrug" title="Prodrug – German" lang="de" hreflang="de" data-title="Prodrug" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%81%CE%BF%CF%86%CE%AC%CF%81%CE%BC%CE%B1%CE%BA%CE%B1" title="Προφάρμακα – Greek" lang="el" hreflang="el" data-title="Προφάρμακα" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Prof%C3%A1rmaco" title="Profármaco – Spanish" lang="es" hreflang="es" data-title="Profármaco" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Profarmako" title="Profarmako – Basque" lang="eu" hreflang="eu" data-title="Profarmako" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%DB%8C%D8%B4%E2%80%8C%D8%AF%D8%A7%D8%B1%D9%88" title="پیش‌دارو – Persian" lang="fa" hreflang="fa" data-title="پیش‌دارو" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Prodrogue" title="Prodrogue – French" lang="fr" hreflang="fr" data-title="Prodrogue" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%84%EB%A1%9C%EB%93%9C%EB%9F%AC%EA%B7%B8" title="프로드러그 – Korean" lang="ko" hreflang="ko" data-title="프로드러그" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%86%D5%A1%D5%AD%D5%A1%D5%A4%D5%A5%D5%B2" title="Նախադեղ – Armenian" lang="hy" hreflang="hy" data-title="Նախադեղ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Bakal_obat" title="Bakal obat – Indonesian" lang="id" hreflang="id" data-title="Bakal obat" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Profarmaco" title="Profarmaco – Italian" lang="it" hreflang="it" data-title="Profarmaco" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%93%D7%9D-%D7%AA%D7%A8%D7%95%D7%A4%D7%94" title="קדם-תרופה – Hebrew" lang="he" hreflang="he" data-title="קדם-תרופה" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Prodroga_farmaceutega" title="Prodroga farmaceutega – Lombard" lang="lmo" hreflang="lmo" data-title="Prodroga farmaceutega" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Prodrug" title="Prodrug – Hungarian" lang="hu" hreflang="hu" data-title="Prodrug" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BB%D0%B5%D0%BA" title="Пролек – Macedonian" lang="mk" hreflang="mk" data-title="Пролек" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Prodrug" title="Prodrug – Dutch" lang="nl" hreflang="nl" data-title="Prodrug" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%97%E3%83%AD%E3%83%89%E3%83%A9%E3%83%83%E3%82%B0" title="プロドラッグ – Japanese" lang="ja" hreflang="ja" data-title="プロドラッグ" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Prodrug" title="Prodrug – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Prodrug" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Prolek" title="Prolek – Polish" lang="pl" hreflang="pl" data-title="Prolek" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Pr%C3%B3-f%C3%A1rmaco" title="Pró-fármaco – Portuguese" lang="pt" hreflang="pt" data-title="Pró-fármaco" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Promedicament" title="Promedicament – Romanian" lang="ro" hreflang="ro" data-title="Promedicament" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BB%D0%B5%D0%BA%D0%B0%D1%80%D1%81%D1%82%D0%B2%D0%B0" title="Пролекарства – Russian" lang="ru" hreflang="ru" data-title="Пролекарства" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Predzdravilo" title="Predzdravilo – Slovenian" lang="sl" hreflang="sl" data-title="Predzdravilo" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Prolek" title="Prolek – Serbian" lang="sr" hreflang="sr" data-title="Prolek" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Prolek" title="Prolek – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Prolek" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Aihiol%C3%A4%C3%A4ke" title="Aihiolääke – Finnish" lang="fi" hreflang="fi" data-title="Aihiolääke" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Prodrog" title="Prodrog – Swedish" lang="sv" hreflang="sv" data-title="Prodrog" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%82%E0%B8%9B%E0%B8%A3%E0%B8%94%E0%B8%A3%E0%B8%B1%E0%B8%81" title="โปรดรัก – Thai" lang="th" hreflang="th" data-title="โปรดรัก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C3%96n_ila%C3%A7" title="Ön ilaç – Turkish" lang="tr" hreflang="tr" data-title="Ön ilaç" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BB%D1%96%D0%BA" title="Пролік – Ukrainian" lang="uk" hreflang="uk" data-title="Пролік" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Ti%E1%BB%81n_ch%E1%BA%A5t" title="Tiền chất – Vietnamese" lang="vi" hreflang="vi" data-title="Tiền chất" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%89%8D%E4%BD%93%E8%8D%AF%E7%89%A9" title="前体药物 – Chinese" lang="zh" hreflang="zh" data-title="前体药物" data-language-autonym="中文" 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<div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Compound that is metabolized into a pharmacologically active drug</div> <p>A <b>prodrug</b> is a pharmacologically inactive <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">medication</a> or compound that, after <a href="/wiki/Drug_administration" class="mw-redirect" title="Drug administration">intake</a>, is <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolized</a> (i.e., converted within the body) into a <a href="/wiki/Pharmacologically_active" class="mw-redirect" title="Pharmacologically active">pharmacologically active</a> drug.<sup id="cite_ref-:0_1-0" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hacker2_2-0" class="reference"><a href="#cite_note-Hacker2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug is absorbed, distributed, metabolized, and excreted (<a href="/wiki/ADME" title="ADME">ADME</a>).<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Prodrugs are often designed to improve <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> when a drug itself is poorly absorbed from the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a>.<sup id="cite_ref-Hacker2_2-1" class="reference"><a href="#cite_note-Hacker2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> A prodrug may be used to improve how selectively the drug interacts with cells or processes that are not its intended target. This reduces adverse or unintended effects of a drug, especially important in treatments like <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a>, which can have severe unintended and undesirable side effects. </p> <style data-mw-deduplicate="TemplateStyles:r1224211176">.mw-parser-output .quotebox{background-color:#F9F9F9;border:1px solid #aaa;box-sizing:border-box;padding:10px;font-size:88%;max-width:100%}.mw-parser-output .quotebox.floatleft{margin:.5em 1.4em .8em 0}.mw-parser-output .quotebox.floatright{margin:.5em 0 .8em 1.4em}.mw-parser-output .quotebox.centered{overflow:hidden;position:relative;margin:.5em auto .8em auto}.mw-parser-output .quotebox.floatleft span,.mw-parser-output .quotebox.floatright span{font-style:inherit}.mw-parser-output .quotebox>blockquote{margin:0;padding:0;border-left:0;font-family:inherit;font-size:inherit}.mw-parser-output .quotebox-title{text-align:center;font-size:110%;font-weight:bold}.mw-parser-output .quotebox-quote>:first-child{margin-top:0}.mw-parser-output .quotebox-quote:last-child>:last-child{margin-bottom:0}.mw-parser-output .quotebox-quote.quoted:before{font-family:"Times New Roman",serif;font-weight:bold;font-size:large;color:gray;content:" “ ";vertical-align:-45%;line-height:0}.mw-parser-output .quotebox-quote.quoted:after{font-family:"Times New Roman",serif;font-weight:bold;font-size:large;color:gray;content:" ” ";line-height:0}.mw-parser-output .quotebox .left-aligned{text-align:left}.mw-parser-output .quotebox .right-aligned{text-align:right}.mw-parser-output .quotebox .center-aligned{text-align:center}.mw-parser-output .quotebox .quote-title,.mw-parser-output .quotebox .quotebox-quote{display:block}.mw-parser-output .quotebox cite{display:block;font-style:normal}@media screen and (max-width:640px){.mw-parser-output .quotebox{width:100%!important;margin:0 0 .8em!important;float:none!important}}</style><div class="quotebox pullquote floatright" style="width:400px; ;"> <div class="quotebox-title" style=""><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> definition</div> <blockquote class="quotebox-quote left-aligned" style=""> <p>Compound that undergoes biotransformation before exhibiting <i>pharmacological</i> effects. </p><p><i>Note 1</i>: Modified from ref.<sup id="cite_ref-IUPAC_5-0" class="reference"><a href="#cite_note-IUPAC-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p><i>Note 2</i>: Prodrugs can thus be viewed as <i>drugs</i> containing specialized nontoxic protective groups used in a transient manner to alter or to eliminate undesirable properties in the parent molecule.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> </blockquote> </div> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prodrug&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many herbal extracts historically used in medicine contain <a href="/wiki/Glycosides" class="mw-redirect" title="Glycosides">glycosides</a> (sugar derivatives) of the active agent, which are hydrolyzed in the intestines to release the active and more bioavailable <a href="/wiki/Aglycone" title="Aglycone">aglycone</a>. For example, <a href="/wiki/Salicin" title="Salicin">salicin</a> is a <a href="/wiki/Glucoside" title="Glucoside">β-D-glucopyranoside</a> that is cleaved by esterases to release <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a>. <a href="/wiki/Aspirin" title="Aspirin">Aspirin</a>, acetylsalicylic acid, first made by <a href="/wiki/Felix_Hoffmann" title="Felix Hoffmann">Felix Hoffmann</a> at <a href="/wiki/Bayer" title="Bayer">Bayer</a> in 1897, is a synthetic prodrug of salicylic acid.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> However, in other cases, such as <a href="/wiki/Codeine" title="Codeine">codeine</a> and <a href="/wiki/Morphine" title="Morphine">morphine</a>, the administered drug is <a href="/wiki/Enzyme" title="Enzyme">enzymatically</a> <a href="/wiki/Bioactivation" class="mw-redirect" title="Bioactivation">activated</a> to form sugar derivatives (morphine-<a href="/wiki/Glucuronides" class="mw-redirect" title="Glucuronides">glucuronides</a>) that are more active than the parent compound.<sup id="cite_ref-Hacker2_2-2" class="reference"><a href="#cite_note-Hacker2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The first synthetic antimicrobial drug, <a href="/wiki/Arsphenamine" title="Arsphenamine">arsphenamine</a>, discovered in 1909 by <a href="/wiki/Sahachiro_Hata" title="Sahachiro Hata">Sahachiro Hata</a> in the laboratory of <a href="/wiki/Paul_Ehrlich" title="Paul Ehrlich">Paul Ehrlich</a>, is not toxic to bacteria until it has been converted to an active form by the body. Likewise, <a href="/wiki/Prontosil" title="Prontosil">prontosil</a>, the first <a href="/wiki/Sulfa_drug" class="mw-redirect" title="Sulfa drug">sulfa drug</a> (discovered by <a href="/wiki/Gerhard_Domagk" title="Gerhard Domagk">Gerhard Domagk</a> in 1932), must be cleaved in the body to release the active molecule, <a href="/wiki/Sulfanilamide" title="Sulfanilamide">sulfanilamide</a>. Since that time, many other examples have been identified. </p><p><a href="/wiki/Terfenadine" title="Terfenadine">Terfenadine</a>, the first non-sedating <a href="/wiki/Antihistamine" title="Antihistamine">antihistamine</a>, had to be withdrawn from the market because of the small risk of a serious side effect. However, terfenadine was discovered to be the prodrug of the active molecule, <a href="/wiki/Fexofenadine" title="Fexofenadine">fexofenadine</a>, which does not carry the same risks as the parent compound. Therefore, fexofenadine could be placed on the market as a safe replacement for the original drug. </p><p><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a>, another non-sedating antihistamine, is the prodrug of <a href="/wiki/Desloratadine" title="Desloratadine">desloratadine</a>, which is largely responsible for the antihistaminergic effects of the parent compound. However, in this case the parent compound does not have the side effects associated with terfenadine, and so both loratadine and its <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a>, desloratadine, are currently marketed.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Recent_prodrugs">Recent prodrugs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prodrug&action=edit&section=2" title="Edit section: Recent prodrugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Approximately 10% of all marketed drugs worldwide can be considered prodrugs. Since 2008, at least 30 prodrugs have been approved by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a>.<sup id="cite_ref-:0_1-1" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Seven prodrugs were approved in 2015 and six in 2017. Examples of recently approved prodrugs are such as <a href="/wiki/Dabigatran_Etexilate" class="mw-redirect" title="Dabigatran Etexilate">dabigatran etexilate</a> (approved in 2010), <a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">gabapentin enacarbil</a> (2011), <a href="/wiki/Sofosbuvir" title="Sofosbuvir">sofosbuvir</a> (2013), <a href="/wiki/Tedizolid_phosphate" class="mw-redirect" title="Tedizolid phosphate">tedizolid phosphate</a> (2014), <a href="/wiki/Isavuconazonium" title="Isavuconazonium">isavuconazonium</a> (2015), <a href="/wiki/Aripiprazole_lauroxil" title="Aripiprazole lauroxil">aripiprazole lauroxil</a> (2015), <a href="/wiki/Selexipag" title="Selexipag">selexipag</a> (2015), <a href="/wiki/Latanoprostene_bunod" title="Latanoprostene bunod">latanoprostene bunod</a> (2017), <a href="/wiki/Benzhydrocodone" title="Benzhydrocodone">benzhydrocodone</a> (2018), <a href="/wiki/Pfizer%E2%80%93BioNTech_COVID-19_vaccine" title="Pfizer–BioNTech COVID-19 vaccine">tozinameran</a> (2020) and <a href="/wiki/Serdexmethylphenidate" title="Serdexmethylphenidate">serdexmethylphenidate</a> (2021). </p> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prodrug&action=edit&section=3" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Prodrugs can be classified into two major types,<sup id="cite_ref-Wu_10-0" class="reference"><a href="#cite_note-Wu-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> based on how the body converts the prodrug into the final active drug form: </p> <ul><li>Type I prodrugs are bioactivated inside the cells (intracellularly). Examples of these are anti-viral nucleoside analogs that must be <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a> and the lipid-lowering statins.</li> <li>Type II prodrugs are bioactivated outside cells (extracellularly), especially in digestive fluids or in the body's <a href="/wiki/Circulatory_system" title="Circulatory system">circulatory system</a>, particularly in the <a href="/wiki/Blood" title="Blood">blood</a>. Examples of Type II prodrugs are salicin (described above) and certain antibody-, gene- or virus-directed enzyme prodrugs used in <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a> or <a href="/wiki/Immunotherapy" title="Immunotherapy">immunotherapy</a>.</li></ul> <p>Both major types can be further categorized into subtypes, based on factors such as (Type I) whether the intracellular bioactivation location is also the site of therapeutic action, or (Type 2) whether or not bioactivation occurs in the gastrointestinal fluids or in the circulation system. </p> <table class="wikitable"> <caption>Classification of prodrugs<sup id="cite_ref-Wu_10-1" class="reference"><a href="#cite_note-Wu-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_11-0" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Type</th> <th>Bioactivation site</th> <th>Subtype</th> <th>Tissue location of bioactivation</th> <th>Examples </th></tr> <tr> <td rowspan="2">Type I</td> <td rowspan="2" align="center">Intracellular</td> <td>Type IA</td> <td>Therapeutic target tissues/cells</td> <td><a href="/wiki/Aciclovir" title="Aciclovir">Aciclovir</a>, <a href="/wiki/Fluorouracil" title="Fluorouracil">fluorouracil</a>, <a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">cyclophosphamide</a>, <a href="/wiki/Diethylstilbestrol_diphosphate" class="mw-redirect" title="Diethylstilbestrol diphosphate">diethylstilbestrol diphosphate</a>, <a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a>, <a href="/wiki/Mercaptopurine" title="Mercaptopurine">mercaptopurine</a>, <a href="/wiki/Mitomycin" class="mw-redirect" title="Mitomycin">mitomycin</a>, <a href="/wiki/Zidovudine" title="Zidovudine">zidovudine</a> </td></tr> <tr> <td>Type IB</td> <td>Metabolic tissues (liver, GI mucosal cell, lung etc.)</td> <td><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a>, <a href="/wiki/Captopril" title="Captopril">captopril</a>, <a href="/wiki/Carisoprodol" title="Carisoprodol">carisoprodol</a>, <a href="/wiki/Heroin" title="Heroin">heroin</a>, <a href="/wiki/Molsidomine" title="Molsidomine">molsidomine</a>, <a href="/wiki/Leflunomide" title="Leflunomide">leflunomide</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Phenacetin" title="Phenacetin">phenacetin</a>, <a href="/wiki/Primidone" title="Primidone">primidone</a>, <a href="/wiki/Psilocybin" title="Psilocybin">psilocybin</a>, <a href="/wiki/Sulindac" title="Sulindac">sulindac</a>, <a href="/wiki/Fursultiamine" title="Fursultiamine">fursultiamine</a> </td></tr> <tr> <td rowspan="3">Type II</td> <td rowspan="3" align="center">Extracellular</td> <td>Type IIA</td> <td>GI fluids</td> <td>Loperamide oxide, <a href="/wiki/Oxyphenisatin" class="mw-redirect" title="Oxyphenisatin">oxyphenisatin</a>, <a href="/wiki/Sulfasalazine" title="Sulfasalazine">sulfasalazine</a> </td></tr> <tr> <td>Type IIB</td> <td>Systemic circulation and other extracellular fluid compartments</td> <td><a href="/wiki/Acetylsalicylate" class="mw-redirect" title="Acetylsalicylate">Acetylsalicylate</a>, <a href="/wiki/Bacampicillin" title="Bacampicillin">bacampicillin</a>, <a href="/wiki/Bambuterol" title="Bambuterol">bambuterol</a>, <a href="/wiki/Chloramphenicol_succinate" class="mw-redirect" title="Chloramphenicol succinate">chloramphenicol succinate</a>, <a href="/wiki/Dipivefrin" class="mw-redirect" title="Dipivefrin">dipivefrin</a>, <a href="/wiki/Fosphenytoin" title="Fosphenytoin">fosphenytoin</a>, <a href="/wiki/Lisdexamfetamine" title="Lisdexamfetamine">lisdexamfetamine</a>, <a href="/wiki/Pralidoxime" title="Pralidoxime">pralidoxime</a> </td></tr> <tr> <td>Type IIC</td> <td>Therapeutic target tissues/cells</td> <td><a href="/wiki/ADEPT_(medicine)" class="mw-redirect" title="ADEPT (medicine)">ADEPTs</a>, <a href="/wiki/GDEPT" class="mw-redirect" title="GDEPT">GDEPTs</a>, <a href="/wiki/VDEPT" class="mw-redirect" title="VDEPT">VDEPTs</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Subtypes">Subtypes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prodrug&action=edit&section=4" title="Edit section: Subtypes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Type IA prodrugs include many antimicrobial and chemotherapy agents (e.g., 5-flurouracil). Type IB agents rely on metabolic enzymes, especially in hepatic cells, to bioactivate the prodrugs intracellularly to active drugs. Type II prodrugs are bioactivated extracellularly, either in the milieu of GI fluids (Type IIA), within the systemic circulation and/or other extracellular fluid compartments (Type IIB), or near therapeutic target tissues/cells (Type IIC), relying on common enzymes such as esterases and phosphatases or target directed enzymes. Importantly, prodrugs can belong to multiple subtypes (i.e., Mixed-Type). A Mixed-Type prodrug is one that is bioactivated at multiple sites, either in parallel or sequential steps. For example, a prodrug, which is bioactivated concurrently in both target cells and metabolic tissues, could be designated as a "Type IA/IB" prodrug (e.g., HMG Co-A reductase inhibitors and some chemotherapy agents; note the symbol " / " applied here). When a prodrug is bioactivated sequentially, for example initially in GI fluids then systemically within the target cells, it is designated as a "Type IIA-IA" prodrug (e.g., <a href="/wiki/Tenofovir_disoproxil" title="Tenofovir disoproxil">tenofovir disoproxil</a>; note the symbol " - " applied here). Many antibody- virus- and gene-directed enzyme prodrug therapies (<a href="/wiki/ADEPT_(medicine)" class="mw-redirect" title="ADEPT (medicine)">ADEPTs</a>, <a href="/wiki/VDEPT" class="mw-redirect" title="VDEPT">VDEPTs</a>, <a href="/wiki/GDEPT" class="mw-redirect" title="GDEPT">GDEPTs</a>) and proposed <a href="/wiki/Nanoparticle" title="Nanoparticle">nanoparticle</a>- or nanocarrier-linked drugs can understandably be Sequential Mixed-Type prodrugs. To differentiate these two Subtypes, the symbol dash " - " is used to designate and to indicate sequential steps of bioactivation, and is meant to distinguish from the symbol slash " / " used for the Parallel Mixed-Type prodrugs.<sup id="cite_ref-:1_11-1" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wu2_12-0" class="reference"><a href="#cite_note-Wu2-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prodrug&action=edit&section=5" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursor (chemistry)</a></li> <li><a href="/wiki/Toxication" title="Toxication">Toxication</a></li> <li><a href="/wiki/Neurotransmitter_prodrug" title="Neurotransmitter prodrug">Neurotransmitter prodrug</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prodrug&action=edit&section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-:0-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFRautioMeanwellDiHageman2018" class="citation journal cs1">Rautio J, Meanwell NA, Di L, Hageman MJ (August 2018). 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Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527321094" title="Special:BookSources/978-3527321094"><bdi>978-3527321094</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Acetylsalicylic+acid&rft.pub=Wiley&rft.date=2009&rft.isbn=978-3527321094&rft.aulast=Schr%C3%B6r&rft.aufirst=Karsten&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dgw6yR6qZe5wC%26q%3DFelix%2BHoffmann%2BBayer%2BArthur%2BEichengr%25C3%25BCn%26pg%3DPA7&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProdrug" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text">UK Medicines Information Pharmacists Group. <a rel="nofollow" class="external text" href="http://www.ukmi.nhs.uk/NewMaterial/html/docs/desloratadine.pdf">New Medicines on the Market: Desloratadine.</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20071011230501/http://www.ukmi.nhs.uk/NewMaterial/html/docs/desloratadine.pdf">Archived</a> 2007-10-11 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> June 2001.</span> </li> <li id="cite_note-Wu-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wu_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wu_10-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWu2009" class="citation journal cs1">Wu KM (October 2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3978533">"A New Classification of Prodrugs: Regulatory Perspectives"</a>. <i>Pharmaceuticals</i>. <b>2</b> (3): 77–81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fph2030077">10.3390/ph2030077</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3978533">3978533</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27713225">27713225</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmaceuticals&rft.atitle=A+New+Classification+of+Prodrugs%3A+Regulatory+Perspectives&rft.volume=2&rft.issue=3&rft.pages=77-81&rft.date=2009-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3978533%23id-name%3DPMC&rft_id=info%3Apmid%2F27713225&rft_id=info%3Adoi%2F10.3390%2Fph2030077&rft.aulast=Wu&rft.aufirst=KM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3978533&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProdrug" class="Z3988"></span></span> </li> <li id="cite_note-:1-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWuFarrelly2007" class="citation journal cs1">Wu KM, Farrelly JG (July 2007). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1259393">"Regulatory perspectives of Type II prodrug development and time-dependent toxicity management: nonclinical Pharm/Tox analysis and the role of comparative toxicology"</a>. <i>Toxicology</i>. <b>236</b> (1–2): 1–6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tox.2007.04.005">10.1016/j.tox.2007.04.005</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17507137">17507137</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicology&rft.atitle=Regulatory+perspectives+of+Type+II+prodrug+development+and+time-dependent+toxicity+management%3A+nonclinical+Pharm%2FTox+analysis+and+the+role+of+comparative+toxicology&rft.volume=236&rft.issue=1%E2%80%932&rft.pages=1-6&rft.date=2007-07&rft_id=info%3Adoi%2F10.1016%2Fj.tox.2007.04.005&rft_id=info%3Apmid%2F17507137&rft.aulast=Wu&rft.aufirst=KM&rft.au=Farrelly%2C+JG&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1259393&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProdrug" class="Z3988"></span>; Table 1</span> </li> <li id="cite_note-Wu2-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wu2_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWu2009" class="citation journal cs1">Wu KM (October 2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3978533">"A New Classification of Prodrugs: Regulatory Perspectives"</a>. <i>Pharmaceuticals</i>. <b>2</b> (3): 77–81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fph2030077">10.3390/ph2030077</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3978533">3978533</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27713225">27713225</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmaceuticals&rft.atitle=A+New+Classification+of+Prodrugs%3A+Regulatory+Perspectives&rft.volume=2&rft.issue=3&rft.pages=77-81&rft.date=2009-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3978533%23id-name%3DPMC&rft_id=info%3Apmid%2F27713225&rft_id=info%3Adoi%2F10.3390%2Fph2030077&rft.aulast=Wu&rft.aufirst=KM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3978533&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProdrug" class="Z3988"></span>; Table 1</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prodrug&action=edit&section=7" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" 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illegal drug selling</a></li> <li><a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">Clandestine chemistry</a></li> <li><a href="/wiki/Lacing_(drugs)" title="Lacing (drugs)">Lacing</a></li></ul></li> <li>Medicines <ul><li><a href="/wiki/Counterfeit_medications" title="Counterfeit medications">Counterfeit medications</a></li> <li><a href="/wiki/List_of_medicine_contamination_incidents" title="List of medicine contamination incidents">List of medicine contamination incidents</a></li></ul></li> <li><a href="/wiki/Impurity" class="mw-redirect" title="Impurity">Impurity</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Harm_reduction" title="Harm reduction">Harm reduction</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Drug_checking" title="Drug checking">Drug checking</a></li> <li><a href="/wiki/Reagent_testing" title="Reagent testing">Reagent testing</a> (<a href="/wiki/List_of_reagent_testing_color_charts" title="List of reagent testing color charts">List of reagent testing color charts</a>)</li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Prodrug&oldid=1244790925">https://en.wikipedia.org/w/index.php?title=Prodrug&oldid=1244790925</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Pharmacokinetics" title="Category:Pharmacokinetics">Pharmacokinetics</a></li><li><a href="/wiki/Category:Prodrugs" 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